Quinoline → 1-methyl-1H-indole-7-carboxylic acid

HRID 1067766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067766
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[C:3]1C(O)=O.N1C2C(=CC=CC=2)C=CC=1>[Cu]=O.Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[CH:3]1

Komponenten

5

Edukt 2

HCID 7047QuinolineHCID 108465121-methylindole-2,7-dicarboxylic Acid

Produkt 1

HCID 183883621-methyl-1H-indole-7-carboxylic acidAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 4.60 g (21.0 mmol) of 1-methyl-indole-2,7-dicarboxylic acid, 0.5 g of copper (II) oxide and 50 ml of quinoline was stirred for an hour with heating at 180° C. After cooling, the reaction mixture was poured onto 200 ml of 2N hydrochloric acid. The mixture was extracted three times with ethyl acetate and the combined extracts were washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 1.82 g (49.0%) of 1-methyl-7-indolecarboxylic acid.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. washthe combined extracts were washed with saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was isolated
  7. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2081eb2cb5c64ed0ae4d86d26dda8249
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248772B1

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